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Why go now?
Trysts in Trieste are beguiling at any time of year, but the advent of winter enhances the heroic melancholy of a city whose heyday is long past. Soon the vast Piazza dell'Unita (1) will be adorned with festive lights and twin Christmas trees. In the first week of December the San Nicolò Christmas Market fills the pedestrianised Viale XX Settembre (2).
Ryanair (0871 246 0000; ryanair.com) flies four times a week in winter from London Stansted to Trieste's airport. Bus 51 ( aptgorizia.it) leaves the airport every half hour (less frequently on Sundays) and covers the 21-mile distance to the bus station (3) on the edge of the city centre in less than an hour. Buy a ticket from machines in the airport arrivals hall for €3.25. Taxis are plentiful and charge about €50.
Get your bearings
A brisk pace will convey you in 15 minutes from the bus station (3) or adjacent Stazione Centrale (4) to Trieste's most impressive landmark, the glorious Piazza dell'Unità (1).
After taking in the swaggering Habsburgian architecture on three sides and the sea on the fourth, visit the welcoming tourist information office (5) at Via dell'Orologio 1 (00 39 040 3478312; turismofvg.it). A maze of steep residential lanes covers the hill of San Giusto. Around the back of the historic hill is the working-class district of San Giacomo. The café-lined Canal Grande (6) is another good landmark.
No two rooms are alike at the Hotel Portacavana (7) at Via Felice Venezian 14 (00 39 040 301313; hotelportacavana.it), though all are cluttered with hand-painted antique furniture. En-suite doubles average €90 without breakfast. The arty L'Albero Nascosto next door at number 18 (00 39 040 300188; alberonascosto.it) has more restrained décor and occupies a carefully restored 18th-century building. Doubles up to €135 including breakfast.
Take a view
To appreciate Trieste's maritime setting, walk out along the Molo Audace (8), then turn back to admire the magnificent scale of the Piazza dell'Unita (1), and to identify the Greek Orthodox church of San Nicolò (9) bracketed by twin palaces. If the libeccio (south-west wind) is blowing across the gulf, the swell may push the water over the stone stanchions lining the wharf.
The narrow lanes of the Jewish ghetto near the Piazza della Borsa (10) are lined with characterful shops selling antiquarian books, engravings and antiques. Wander along Via del Ponte and Piazza Vecchia (11) near the excavated Roman Theatre to find the Libreria Achille Misan at Piazza Vecchia 4 , selling old and new prints.
The Podrecca Glassware shop (12) at Via Mazzini 42a sells folk ceramics from the region.
Lunch on the run
Rebechin is the Triestino dialect approximation to the phrase "lunch on the run". It refers to a snack such as sausage and sauerkraut eaten standing up at one of the "buffet" restaurants scattered around the city.
For something more sophisticated, head for the stylish SaluMare (13) at 13a Via di Cavana which calls itself a laboratorio del pesce; it's open 10.30am-2pm and 5.30-9pm, Tuesday to Saturday. Dainty open-topped sandwiches (tartines) have fillings such as house-smoked fish or tuna and olive paté, and cost a couple of euros. End with a gelato next door at number 15, Chocolat.
A walk in the park
The wedge-shaped Giardino M Tommasini (14) is the liveliest park: small children learn to cycle or skate on the pista di pattinaggi, workers from the surrounding commercial area play table tennis and matrons rest on benches around the central lake.
The Venetian Castle of San Giusto (15) consists of an immense asymmetrical terrace surrounded by fortified walls with towers from different periods. Circumambulating the ramparts confers splendid views. The underground lapidarium in a corner of the courtyard is full of weird and wonderful ancient remains found in Trieste – but may be temporarily closed. The castle opens 9am-5pm daily, admission €4 (including a good audio commentary).
A short stroll away is the imposing Romanesque front of the Cattedrale di San Giusto (16) (7.30am-noon and 2.30-6.30pm Mon-Sat, Sundays 2.30-6.30pm, free). The beautiful 13th-century mosaics in the apse at the end of the left aisle depict the Madonna with child and apostles.
The blackboard list of wines at Osterio Da Marino (17) (Via del Ponte 5; 00 39 040 366 596; www.osteriadamarino.com) includes everything from a glass of Prosecco (€2) to a complex, prize-winning wine from the Carso, Vitovska Vodopivec (€6). Early evening drinkers get superior complimentary snacks (stuzzichini).
Dine with the locals
The Restaurant Arcoriccardo (18) at Via del Trionfo 3a (00 39 040 241 0446; arcoriccardo-ristorante.it; closed Sunday evenings) is next to the 1st-century BC Arco di Riccardo. A full seafood-focused dinner with wine costs about €80 for two.
The intimate enoteca Nettare di Vino (19) at 6B Via Armando Diaz (00 39 040 310 200; closed Sundays) offers regional ingredients such as Friulian ham. Pasta dishes average €6.50, main courses €15.
Sunday morning: go to a synagogue
No expense was spared in the building in 1912 of Trieste's last remaining Synagogue (20) at 19 Via San Francesco (00 39 040 672 6736; triestebraica.it). Guided tours (€3.50) at 10am, 11am and noon every Sunday paint a poignant picture of the once-vigorous Jewish community of cultured merchants dwindling to 20 souls after the war. The richly decorated interior of the grand domed edifice celebrates the once-ascendant minority.
Out to brunch
A Belle Epoque coffeehouse is the perfect place to relax on a Sunday morning. After settling into one of the worn banquettes at a favourite of James Joyce, Caffè San Marco (21) at Via C Battisti 18 (00 39 040 371373), you can delight in the fanciful décor, antique cash register and po-faced waiters as you wait for your "caffè in B" to arrive – a typical Triestine espresso served in a small glass.
A short walk away, the Pasticceria Caffè Pirona (22) at Largo Barriera Vecchia 12 is another place where Joyce indulged himself. Tempting mounds of pastries such as presnitz made with almonds, pine nuts and dried fruit have their culinary roots in central Europe.
Take a ride
For more than a century, a tram has been leaving Piazza Oberdan (23) on the north side of the city, morphing into a funicular when the gradient steepens to one-in-four. Slowly and noisily the historic tranvia ( tramdeopcina.it) ascends the nearly 1,000ft escarpment to the Carso plateau. The 25-minute trip to the village of Villa Opicina costs €1.10.
Take a hike
Several scenic hikes start from the Obelisco tram stop just before the Opicina terminus. The Sentiero Napoleonico is a wide, tame path through reforested pine, hornbeam and linden. It follows the karst edge for a couple of miles. Facing the winter sun, it affords splendid panoramic views over the city and gulf.
Icing on the cake
Like a building yearning to set sail, the Castle at Miramare teeters on the edge of a promontory five miles west of Trieste; take bus 36 from Piazza Oberdan (23). Miramare brings to life the tale of the romantic Archduke Ferdinand Maximilian who built his dream home in the middle of the 19th century but never lived in it. See this ill-fated place at sunset; open 9am-7pm; €6.